Methanol → HCID 70000907, Verbindung

HRID 1264384Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1264384
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([N:10]([C:12](=[O:26])[CH2:13][N:14]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])[CH3:15])[CH3:11])=[CH:6][CH:5]=1.CO>C1COCC1>[CH2:19]([O:18][C:16](=[O:17])[N:14]([CH2:13][C:12](=[O:26])[N:10]([C:7]1[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][CH:6]=1)[CH3:11])[CH3:15])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 70002203HCID 70002203, Verbindung

Produkt 1

HCID 70000907HCID 70000907, VerbindungAusbeute 52,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

Under argon 742.7 mg (32.4 mmol, 1.5 eq) lithium borhydride in 35 ml THF were added dropwise to 8 g (21.6 mmol) 4-[[(Benzyloxycarbonyl-methyl-amino)-acetyl]-methyl-amino]-benzoic acid methyl ester in 100 ml THF at RT. The suspension was stirred at RT over night, heated to 50° C. for 3.25 h, recooled to RT and 21 ml MeOH were added slowly. The solution was added to ice water, extracted with ether (3×), the combined organic layers were washed with water, dried over MgSO4, filtered and evaporated. The crude product was purified by flash chromatography on silica gel with a gradient of CH2Cl2/MeOH (100:0-99.9:0.1) yielding 3.9 g (52%) {[(4-Hydroxymethyl-phenyl)-methyl-carbamoyl]-methyl}-methyl-carbamic acid benzyl ester as yellow oil (Rf 0.4 CH2Cl2:MeOH 9:1), MS: 343 (MH+).

Aufarbeitung

  1. temperatureheated to 50° C. for 3.25 h
  2. customrecooled to RT
  3. extractionextracted with ether (3×)
  4. washthe combined organic layers were washed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on silica gel with a gradient of CH2Cl2/MeOH (100:0-99.9:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-8c8b545bfbcb4de69235644467588e02
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541638B2

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